EP0535490B1 - Azofarbstoffe enthaltende Polymerisate - Google Patents

Azofarbstoffe enthaltende Polymerisate Download PDF

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Publication number
EP0535490B1
EP0535490B1 EP92116096A EP92116096A EP0535490B1 EP 0535490 B1 EP0535490 B1 EP 0535490B1 EP 92116096 A EP92116096 A EP 92116096A EP 92116096 A EP92116096 A EP 92116096A EP 0535490 B1 EP0535490 B1 EP 0535490B1
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EP
European Patent Office
Prior art keywords
formula
mol
monomer units
hydrogen
alkoxy
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP92116096A
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German (de)
English (en)
French (fr)
Other versions
EP0535490A2 (de
EP0535490A3 (enrdf_load_stackoverflow
Inventor
Matthias Dr. Wiesenfeldt
Sabine Dr. Gruettner-Merten
Ruediger Dr. Sens
Karl-Heinz Dr. Etzbach
Heike Dr. Kilburg
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BASF SE
Original Assignee
BASF SE
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Publication date
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Publication of EP0535490A3 publication Critical patent/EP0535490A3/xx
Application granted granted Critical
Publication of EP0535490B1 publication Critical patent/EP0535490B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F246/00—Copolymers in which the nature of only the monomers in minority is defined
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
    • C09B69/106—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an azo dye
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/35—Non-linear optics
    • G02F1/355—Non-linear optics characterised by the materials used
    • G02F1/361—Organic materials
    • G02F1/3611—Organic materials containing Nitrogen
    • G02F1/3612—Heterocycles having N as heteroatom
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/35—Non-linear optics
    • G02F1/355—Non-linear optics characterised by the materials used
    • G02F1/361—Organic materials
    • G02F1/3613—Organic materials containing Sulfur
    • G02F1/3614—Heterocycles having S as heteroatom
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/35—Non-linear optics
    • G02F1/355—Non-linear optics characterised by the materials used
    • G02F1/361—Organic materials
    • G02F1/3615—Organic materials containing polymers
    • G02F1/3617—Organic materials containing polymers having the non-linear optical group in a side chain

Definitions

  • WO-A 91/09842 describes polymers containing benzothiazole or thienothiazole azo chromophores which have non-linear optical properties.
  • radicals D in formula I which come from a heterocyclic amine from the pyrrole, thiophene, pyrazole, isothiazole, triazole, thiadiazole, benzthiophene, benzisothiazole, pyridothiophene, pyrimidothiophene or tienothiophene series .
  • C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or halogen, in particular chlorine or bromine, can be used as substituents.
  • the phenyl rings generally have 1 to 3 substituents.
  • R 1 , R 2 , R 3 , L 2 , L 4 , L 5 , L 9 , L 11 and L 12 are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, pentyl, isopentyl, Neopentyl, tert-pentyl, hexyl or 2-methyl pentyl.
  • R 2 radicals are furthermore, for example, formylamino, acetylamino, propionylamino or butyrylamino.
  • L 9 radicals are also, for example, benzyl or 1- or 2-phenylethyl.
  • L 2 , L 9 and L 11 are furthermore, for example, methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, pentylthio, hexylthio, benzylthio or 1- or 2-phenylethylthio.
  • L 2 radicals are also, for example, phenylthio, 2-methylphenylthio, 2-methoxyphenylthio or 2-chlorophenylthio.
  • Residues R 1 , R 2 and L 2 are furthermore, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, pentyloxy, isopentyloxy, neopentyloxy, tert-pentyloxy, hexyloxy or 2- Methylpentyloxy.
  • L 2 and L 13 are also, for example, fluorine, chlorine or bromine.
  • L 1 and L 2 are also, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl, pentylsulfonyl, isopentylsulfonyl, Neopentylsulfonyl, hexylsulfonyl, phenylsulfonyl, 2-methylphenylsulfonyl, 2-methoxyphenylsulfonyl or 2-chlorophenylsulfonyl.
  • L 6 like L 3 , are also, for example, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl or sec-butoxycarbonyl.
  • R 1 , R 2 and L 2 are furthermore, for example, 2-methoxyethoxy, 2-ethoxyethoxy, 2- or 3-methoxypropoxy, 2- or 3-ethoxypropoxy, 2- or 4-methoxybutoxy, 2- or 4-ethoxybutoxy, 5- Methoxypentyloxy, 5-ethoxypentyloxy, 6-methoxyhexyloxy, 6-ethoxyhexyloxy, benzyloxy or 1- or 2-phenylethoxy.
  • Residues X are still e.g. Methylamino, ethylamino, propylamino, isopropylamino or butylamino.
  • L 11 and X are also, for example, dimethylamino, diethylamino, dipropylamino, diisopropylamino or N-methyl-N-ethylamino.
  • L 12 radicals are furthermore, for example, 2-methoxycarbonylethylthio or 2-ethoxycarbonylethylthio.
  • R 3 radicals are furthermore, for example, cyclopentyl, cyclohexyl, cycloheptyl, allyl or methallyl.
  • L 9 radicals are furthermore, for example, phenyl, 2-, 3- or 4-methylphenyl, 2,4-dimethylphenyl, 2-, 3- or 4-chlorophenyl, 2-, 3- or 4-methoxyphenyl, 2- or 3-methylthienyl or 2-, 3- or 4-methylpyridyl.
  • Residues Y 1 and Y 2 are, for example, (CH 2 ) 2 , (CH 2 ) 3 , (CH 2 ) 4 , (CH 2 ) 5 , (CH 2 ) 6 , (CH 2 ) 7 , (CH 2 ) 8 , (CH 2 ) 9 , (CH 2 ) 10 , CH (CH 3 ) -CH 2 , CH (CH 3 ) -CH (CH 3 ), C 2 H 4 -OC 2 H 4 , C 2 H 4 -NH- C 2 H 4 , C 2 H 4 -N (CH 3 ) -C 2 H 4 , C 2 H 4 OC 2 H 4 -OC 2 H 4 , C 2 H 4 -NH-C 2 H 4 -NH-C 2 H 4 or C 2 H 4 -N (CH 3 ) -C 2 H 4 -N (CH 3 ) -C 2 H 4 .
  • Residues W are e.g. Methylimino, ethylimino, propylimino, isopropylimino or butylimino.
  • L 1 and L 6 are, for example, formyl, acetyl, propionyl, butyryl, pentanoyl or hexanoyl.
  • the remainder is derived from compounds of the formula VIIa, VIIb or VIIc, in which Z 1 is cyano, C 1 -C 4 alkanoyl, C 1 -C 4 alkoxycarbonyl or C 3 -C 4 alkenyloxycarbonyl, Z 2 C 1 -C 4 alkyl, C 1 -C 4 alkoxy or C 3 -C 4 alkenyloxy, Z 3 C 1 -C 4 alkoxycarbonyl or C 3 -C 4 alkenyloxycarbonyl and Z 4 mean cyano.
  • Z 1 is cyano, C 1 -C 4 alkoxycarbonyl or C 3 -C 4 alkenyloxycarbonyl, Z 2 C 1 -C 4 alkoxy or C 2 -C 4 alkenyloxy, Z 3 C 1 -C 4 alkoxycarbonyl or C 3 -C 4 alkenyloxycarbonyl and Z 4 mean cyano.
  • Polymers containing azo dyes are preferred which, as characteristic monomer units, are residues of the formula Ia wherein D, R 1 , R 2 , R 3 , R 4 , Y 1 and W each have the abovementioned meaning and have the abovementioned formula II.
  • polymers containing azo dyes in which D in formula I is derived from an amine of the formula VIa, VIb, VIc, VIe, VIf, VIm or VIn are also preferred.
  • polymers containing azo dyes in which the proportion of the monomer units of the formula I is 4 to 50, in particular 8 to 25, mol%, that of the formula II 51 to 96, in particular 75 to 92 mol%, that of the formula III 0 to 30, in particular 0 to 15 mol% and that of the formula IV 0 to 50, in particular 0 to 20 mol%, in each case based on the polymer, and the average molecular weight of the polymer 1500 to 50,000, in particular 2000 to 25,000.
  • Polymers containing azo dyes are particularly preferred in which D is derived from amines from the thiophene series, in particular from those of the formula VIb.
  • azo dyes of the formula V are advantageously used suitable in which D, R 1 , R 2 , R 3 , R 4 , Y 1 and W each have the abovementioned meaning.
  • the new polymers can be prepared by methods known per se, as described, for example, in J. Polymer Sci. (loc. cit.) are described.
  • an azo dye of the formula V with an acrylic compound of the formula VIII in which R 4 and X each have the abovementioned meaning, styrene and a cinnamic acid ester of the formula IX in which Y 2 and R 4 each have the abovementioned meaning, in the abovementioned molar ratio in an inert solvent (for example toluene or xylene) in the presence of a radical initiator (for example azo-bis-isobutyronitrile).
  • an inert solvent for example toluene or xylene
  • a radical initiator for example azo-bis-isobutyronitrile
  • the azo dyes of formula V are known per se and e.g. in EP-A-201 896, DE-A-3 108 077, US-A-4 843 153 or GB-A-1 546 803 or can be obtained by the methods mentioned therein.
  • the polymers containing azo dyes are advantageously suitable for use in nonlinear optical systems (see, for example, Chemistry and Industry, Oct. 1, 1990, pages 600 to 608).
  • the radicals L 8 correspond to the radicals mentioned in detail for L 2 .
  • L 8 radicals are furthermore, for example, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl or sec-butoxycarbonyl.
  • the residues L 7 correspond to the residues mentioned in detail for L 1 .
  • polymers containing azo dyes are preferred which have residues of the formula Xa as characteristic monomer units wherein D 1 , R 1 , R 2 , R 3 , R 4 , Y 1 and W each have the abovementioned meaning and have the abovementioned formula II.
  • the polymers containing azo dyes which are particularly preferred for use in nonlinear optics are those already mentioned as preferred above and those in which D is derived from amines of the thiazole series, the amines of the thiazole series having the same meaning as the amines of the thiophene series.
  • Layers containing the polymers according to the invention are produced in a manner known per se, e.g. by wet coating (spin coating) with a 5 to 15% by weight solution of the polymer in a solvent (e.g. tetrachloroethane, methylene chloride or tetrahydrofuran).
  • a solvent e.g. tetrachloroethane, methylene chloride or tetrahydrofuran.
  • the new polymers can also be crosslinked photochemically, thermally or by the action of electron beams.
  • the new polymers are characterized by good processability into thin layers, high purity, narrow molecular weight distribution, good orientation in the electrical field, good long-term stability, high glass levels and a high electro-optical coefficient.
  • a monomer solution consisting of m mol% of dye monomer and l + p + q mol% of comonomer in absolute toluene was mixed with 2 mol% of azo-bis-isobutyronitrile. After argon had been passed through for 10 minutes, the monomer mixture was thermostabilized at 50.degree. The polymerization reaction was complete after 100 hours. The polymers were precipitated with methanol and reprecipitated twice from hexane / methanol.

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  • Physics & Mathematics (AREA)
  • Nonlinear Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Plural Heterocyclic Compounds (AREA)
EP92116096A 1991-10-01 1992-09-21 Azofarbstoffe enthaltende Polymerisate Expired - Lifetime EP0535490B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4132685 1991-10-01
DE4132685A DE4132685A1 (de) 1991-10-01 1991-10-01 Azofarbstoffe enthaltende polymerisate

Publications (3)

Publication Number Publication Date
EP0535490A2 EP0535490A2 (de) 1993-04-07
EP0535490A3 EP0535490A3 (enrdf_load_stackoverflow) 1994-02-16
EP0535490B1 true EP0535490B1 (de) 1997-06-04

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ID=6441914

Family Applications (1)

Application Number Title Priority Date Filing Date
EP92116096A Expired - Lifetime EP0535490B1 (de) 1991-10-01 1992-09-21 Azofarbstoffe enthaltende Polymerisate

Country Status (4)

Country Link
US (4) US5264507A (enrdf_load_stackoverflow)
EP (1) EP0535490B1 (enrdf_load_stackoverflow)
JP (1) JPH05239374A (enrdf_load_stackoverflow)
DE (2) DE4132685A1 (enrdf_load_stackoverflow)

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Publication number Priority date Publication date Assignee Title
FR2690453B1 (fr) * 1992-04-25 1995-11-03 Sandoz Sa Nouveaux composes polymeres ayant des proprietes optiques non lineaires.
DE4218359A1 (de) * 1992-06-04 1993-12-09 Basf Ag Polymerisate, die Methin- oder Azamethinfarbstoffe enthalten
US5290887A (en) * 1993-04-30 1994-03-01 The Dow Chemical Company Epoxy resins containing thiadiazole and/or oxadiazole moieties
DE4317094A1 (de) * 1993-05-21 1994-11-24 Basf Ag Polyester mit nichtlinear optischen Chromophoren und deren Verwendung
DE4317095A1 (de) * 1993-05-21 1994-11-24 Basf Ag Verfahren zur Polung und Orientierung von organischen Materialien, die nichtlinear optische Chromophore enthalten, und deren Verwendung
WO1995002848A1 (en) * 1993-07-12 1995-01-26 Minnesota Mining And Manufacturing Company Multifunctional azo compounds and polymers derived therefrom for nonlinear optics
US5387657A (en) * 1993-09-10 1995-02-07 The Dow Chemical Company Epoxy resins containing thiadiazole and/or oxadiazole moieties
DE4333291A1 (de) * 1993-09-30 1995-04-06 Basf Ag Verwendung von Azofarbstoffen in der nichtlinearen Optik
DE4335496A1 (de) * 1993-10-19 1995-04-20 Basf Ag Diphenylaminverbindungen
DE4339712A1 (de) * 1993-11-22 1995-05-24 Basf Ag Thienothienylazoaniline in der nichtlinearen Optik
DE4401911A1 (de) * 1994-01-24 1995-08-03 Basf Ag Verwendung von Aryl- oder Heteroarylazoanilinen in der nichtlinearen Optik
DE19521503A1 (de) * 1995-06-13 1996-12-19 Basf Ag Polymerisierbare Azofarbstoffe mit Thiophenstruktur
DE19525304A1 (de) * 1995-07-12 1997-01-16 Basf Ag Copolymere mit Adamantyl- und Farbstoffseitenketten
GB2305928A (en) * 1995-10-06 1997-04-23 Coates Brothers Plc Coloured hot melt ink jet vehicle
ES2176739T3 (es) * 1996-05-22 2002-12-01 Bayer Ag Sustratos rapidamente fotodireccionables, asi como polimeros con grupos laterales fotodireccionables con una elevada birrefringencia inducible.
TW406215B (en) * 1996-08-07 2000-09-21 Fuji Photo Film Co Ltd Composition for anti-reflective coating material in lithographic process, and process for forming resist pattern
US5726145A (en) * 1996-08-26 1998-03-10 Colgate-Palmolive Company Color perfume concentrates
KR20000057281A (ko) * 1996-11-27 2000-09-15 해리 제이. 그윈넬 광흡수 중합체성 조성물의 제조 방법
EP0856527A1 (de) * 1997-01-29 1998-08-05 Bayer Ag Photoadressierbare Seitengruppenpolymere mit hoher induzierbarer Doppelbrechung
DE19754025A1 (de) 1997-12-05 1999-06-10 Basf Ag Farbstoffzubereitungen, enthaltend Azofarbstoffe
US6429023B1 (en) 1998-07-20 2002-08-06 Shayda Technologies, Inc. Biosensors with polymeric optical waveguides
US6661942B1 (en) 1998-07-20 2003-12-09 Trans Photonics, Llc Multi-functional optical switch (optical wavelength division multiplexer/demultiplexer, add-drop multiplexer and inter-connect device) and its methods of manufacture
GB9827894D0 (en) * 1998-12-21 1999-02-10 Zeneca Ltd Composition
AU2002213362A1 (en) 2000-10-19 2002-04-29 Trans Photonics, L.L.C. Novel substituted-polyaryl chromophoric compounds
JP4868493B2 (ja) * 2004-08-13 2012-02-01 独立行政法人産業技術総合研究所 ヘテロ環アゾ化合物による光応答性材料とそれを用いた光情報記録媒体

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FR1468540A (fr) * 1966-02-18 1967-02-03 Basf Ag Couleurs d'impression pour l'impression d'objets à surface lisse
US3507850A (en) * 1966-05-25 1970-04-21 Du Pont Polymeric fugitive azo dyes derived from methacrylate alkyl ester,methacrylic acid and a dye monomer containing sulfonic acid groups and a methacryloyl group
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US5061404A (en) * 1989-12-26 1991-10-29 Allied-Signal Inc. Electro-optical materials and light modulator devices containing same

Also Published As

Publication number Publication date
DE59208569D1 (de) 1997-07-10
JPH05239374A (ja) 1993-09-17
EP0535490A2 (de) 1993-04-07
US5461131A (en) 1995-10-24
US5434231A (en) 1995-07-18
US5264507A (en) 1993-11-23
DE4132685A1 (de) 1993-04-08
USRE35407E (en) 1996-12-17
EP0535490A3 (enrdf_load_stackoverflow) 1994-02-16

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